Podcast Summary

Podcast: How To Fail With Elizabeth Day
Episode: ON EMBARRASSING MOMENTS… With Dan Levy and Phoebe Waller-Bridge
Date: November 3, 2025
Host: Elizabeth Day
Guests: Phoebe Waller-Bridge, Dan Levy

Episode Overview

This special archive episode dives into the theme of public humiliation and embarrassing moments, revisiting two of the podcast’s most beloved and hilarious stories. Host Elizabeth Day brings back viral tales from writer-actress Phoebe Waller-Bridge and actor-writer Dan Levy, exploring what these embarrassing failures taught them about self-acceptance, humor, and personal growth. The episode maintains a comedic, honest tone, celebrating vulnerability and learning through shared human awkwardness.

Key Discussion Points & Insights

1. Phoebe Waller-Bridge and the Apple Crumble Incident

[02:55 – 05:55]

• Setting the Scene: During filming of The Iron Lady, Phoebe was starstruck working with Meryl Streep, who was in full prosthetic makeup and remained largely silent and focused on set.

  • Phoebe confesses:
    "I go weird around celebrities and always very in a very individual way for each celebrity. I should just not be around them." [02:55]

• The Moment: One day, Meryl breaks character and, in her Margaret Thatcher voice, asks the room how everyone’s day is going, surprising the cast and crew.

• Phoebe’s Triumph & Downfall:

  • Phoebe manages to make Meryl laugh with a joke and feels triumphant:
    "And everyone else looked at me with such steel and an ashen face and fury. And I was like, I've won it. She's mine." [04:11]
  • Later, at lunch, Meryl approaches Phoebe, who is eating apple crumble, and asks what she's eating.
  • Overexcited, Phoebe flings the pudding all over herself:
    "I flung my apple crumble straight into my chest, my costume chest." [05:01]
  • Meryl assures her, “I wasn’t gonna take it from you,” before walking away, leaving Phoebe mortified, clutching messy apple crumble to her silk shirt.

• Memorable Quote:
  Phoebe Waller-Bridge:

  "I literally squawked my apple crumble. And she went, 'Oh.' And then she went back into her American accent, which she hadn't done for the whole time, and she went, 'I wasn't gonna take it from you.'" [05:04]

2. Dan Levy and the Birthday Cake Disaster

[06:10 – 09:13]

• Childhood Humiliation: Dan recounts a vivid memory from second grade (age 7-8) in Canada, when his mother brought in a belated birthday cake for him to share at school.
• The Mishap:
  • Overzealous to impress his classmates and teacher, Dan rushes to carry the cake himself.
  • He trips and the cake falls onto his shoes and the floor. The class erupts in laughter.
  • Flustered and panicked, he begins to eat cake off his shoes—a spontaneous, embarrassed reaction.
  • The moment lingers in his memory, representing not just physical but emotional awkwardness.
  • Dan reflects:
    "It was the deepest humiliation I'd felt in my young life. And I looked around and didn't know what to do...my reaction was to sort of, I guess, go completely pale in the face and then reach down and start to eat the cake off my shoes." [07:40]
• Insight: This event, for Dan, marks an early feeling of overreaching (hubris) and failing publicly, sticking with him ever since.
• Reflection on School: Both Dan and Elizabeth discuss the difficulties of school as an environment for those hiding their true selves and the lasting impact of childhood embarrassment.
  • Dan:
    "I've never liked school. Not a single day. And I think part of it had to do with the fact that I wasn't the truest expression of myself." [09:13]

3. Coping with Failure, Laughter, and Control

[09:17 – 11:19]

• Turning Humiliation into Humor:
  • Elizabeth notes the repeated theme of childhood embarrassment and its powerful, formative nature.
  • She observes that being laughed at often propels people to seek control over comedic moments later in life—as writers, comedians, or performers.
  • Dan agrees:
    "Of course you want to be in control of when people laugh."
• Comedic Ethics:
  • Dan shares a guiding principle learned from his father and Catherine O'Hara:
    "You can tell very funny jokes about people in celebration of people, but not at their expense. And there's a very fine line between cruel comedy and observational comedy. And I will always lean towards observational comedy." [10:11]
  • He regards the warmth and inclusivity of Schitt’s Creek as the model for comedic storytelling:
    "There was a kind of democracy of comedy across the board. There was no butt of the joke."

Most Memorable Quotes

• Phoebe Waller-Bridge:

  "I just got so excited about the banter with Meryl that I flung my apple crumble straight into my chest, my costume chest." [05:00]

• Meryl Streep (quoted by Phoebe):

  "I wasn't gonna take it from you." [05:09]

• Dan Levy:

  "My reaction was to sort of, I guess, go completely pale in the face and then reach down and start to eat the cake off my shoes. I don't know what that impulse was." [07:45]

• Dan Levy:

  "You can tell very funny jokes about people in celebration of people, but not at their expense." [10:11]

Important Timestamps

• [02:55] Phoebe's apple crumble, Meryl Streep story begins
• [05:00] Phoebe accidentally spills apple crumble all over herself
• [06:10] Dan introduces his second-grade birthday cake humiliation
• [07:45] Dan eats cake off his shoes in a panic
• [09:13] Dan on not enjoying school and hiding his true self
• [10:11] Dan’s philosophy on comedy and jokes

Conclusion

Elizabeth Day’s collection of joyous, honest failures affirms the deeply human experience of social awkwardness and mortification—showing how humor and vulnerability can ultimately connect us, teach us, and empower us to tell our own story. The episode ends with an encouragement to share failures, reminding listeners that “a fail shared is a fail halved.”